(1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
• CAS No.: 4680-24-4
• Deprecated CAS: 942277-71-6
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• UNII: KBX06MQJ5Y
• DSSTox Substance ID: DTXSID10196943
• Nikkaji Number: J350.265A
• Wikidata: Q27093910
• RXCUI: 2556900
• Metabolomics Workbench ID: 55188
• Mol file: 4680-24-4.mol

Synonyms:(1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane;4680-24-4;cis-(+)-Limonene oxide;13837-75-7;(+)-cis-Limonene oxide;KBX06MQJ5Y;(4R)-limonene 1beta,2beta-epoxide;1beta,2beta-epoxy-4betaH-p-menth-8-ene;(1R,4R,6S)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane;rel-(1R,4R,6S)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane;(1R,4R,6S)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane;UNII-KBX06MQJ5Y;(R)-cis-Limonene epoxide;D-LIMONENE 1,2-EPOXIDE;cis-limonene oxide;+(-)-limonene oxide;cis-limonene-1,2-oxide;SCHEMBL2747593;(+)-cis-limonene-1,2-epoxide;CHEBI:35669;DTXSID10196943;1-Methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptane (1alpha,4alpha,6alpha)-(+)-;7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-, (1alpha,4alpha,6alpha)-(+)-;CCEFMUBVSUDRLG-KXUCPTDWSA-N;LIMONENE OXIDE, CIS-(+)-;AKOS006302844;AT23318;DB02924;(+)-(1R,4R)-limonene-1,2- epoxide;BS-46525;FEMA NO. 4655, CIS-(+)-;(+)-(1R,2S,4R)-1,2-epoxy-8-p-menthene;(+)-(1R,2S,4R)-LIMONENE 1,2-EPOXIDE;A921062;Q27093910;7-OXABICYCLO(4.1.0)HEPTANE, 1-METHYL-4-(1-METHYLETHENYL)-, (1R,4R,6S)-

Chemical Property of (1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

Chemical Property:

• Melting Point: >1000 °C
• Refractive Index: n20/D 1.466
• Boiling Point: 113-114 °C(Press: 50 Torr)
• Flash Point: 65 °C
• PSA: 12.53000
• Density: 0.931 g/mL at 20 °C(lit.)
• LogP: 2.52010
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

98% ^*data from raw suppliers

cis-(?)-Limonene oxide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C(C1)O2)C
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@@]2([C@H](C1)O2)C

Technology Process of (1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

There total 67 articles about (1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

(4R)-limonene 1,2-epoxide (1195-92-2) → (1S,2S,4R)-limonene-1,2-diol (1946-00-5,13833-08-4,38630-75-0,39067-95-3,39903-99-6,39904-01-3,39904-04-6,39904-09-1,39904-12-6,57457-97-3,59121-74-3,59121-75-4,59121-76-5,59121-77-6,59121-82-3,76740-41-5) + cis-(R)-limonene oxide (4680-24-4)

Guidance literature:

With tomsk-limonene-1,2-epoxide hydrolase; In aq. phosphate buffer; at 30 ℃; for 24h; pH=8; Enzymatic reaction;

DOI:10.1002/cctc.201500608

Reference yield: 45.4%

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → trans 1,2-limonene epoxide (1195-92-2,4680-24-4,4959-35-7,6909-30-4,13837-75-7,32543-51-4,42477-94-1,66141-65-9,66141-66-0) + (1S,2R,4R)-limonene-1,2-epoxide (6909-30-4)

Guidance literature:

With ammonium acetate; dihydrogen peroxide; In methanol; acetone; Reagent/catalyst; Catalytic behavior;

DOI:10.1016/j.molcata.2016.08.033

Reference yield:

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (R)-2-methyl-2-((R)-4-methylcyclohex-3-enyl)oxirane (28098-67-1,31684-93-2,62660-04-2,62660-05-3,28098-68-2) + (S)-2-methyl-2-((R)-4-methylcyclohex-3-enyl)oxirane (28098-68-2,31684-93-2,62660-04-2,62660-05-3,28098-67-1) + (1S,4R,6R)-1-methyl-4-((R)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane (96-08-2) + (1S,4R,6R)-1-methyl-4-((S)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane (96-08-2) + (1R,4R,6S)-1-methyl-4-(S)-2-methyloxiran-2-yl-7-oxa-bicyclo[4.1.0]heptane (96-08-2) + (1R,4R,6S)-1-methyl-4-((R)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane (96-08-2) + (1S,2R,4R)-limonene-1,2-epoxide (6909-30-4) + cis-(R)-limonene oxide (4680-24-4)

Guidance literature:

With alumina; water; dihydrogen peroxide; In ethyl acetate; at 80 ℃; for 4h; Overall yield = 98.1 %;

DOI:10.1016/j.jcat.2014.08.004

upstream raw materials:

D-limonene

(1R,2S,4R,8R)-1,2-epoxy-8,9-dibromo-p-menthane

(4R)-limonene 1,2-epoxide

dimethyl amine

Downstream raw materials:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

(-)-trans-carveol

p-Menthadiene-<1(7),8>-trans-ol-(2)

Trimethyl-((1R,4S,5R,8R)-8-methyl-4-phenyl-4-phenylsulfanylmethyl-2,3-dioxa-bicyclo[3.3.1]non-8-yloxy)-silane

Refernces

• 1、 Cubillos Lobo, Jairo Antonio,Vargas, Maria,Reyes, Juliana,Villa, Aida,De Correa, Consuelo Montes. "Effect of the substrate and catalyst chirality on the diastereoselective epoxidation of limonene using Jacobsen-type catalysts". . p. 403 - 410. Retrieved 2010.
• 2、 -. "OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF". Paragraph 00665; 00667. . Retrieved 2021/11/26.
• 3、 Maltby, Katarzyna A.,Hutchby, Marc,Plucinski, Pawel,Davidson, Matthew G.,Hintermair, Ulrich. "Selective Catalytic Synthesis of 1,2- and 8,9-Cyclic Limonene Carbonates as Versatile Building Blocks for Novel Hydroxyurethanes". supporting information. p. 7405 - 7415. Retrieved 2020/05/25.